Trifluoroacetic acid → HCID 131732900, compound

HRID 2167111Notes

Reaction equation

HRID 2167111 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][NH2:4].[NH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>C(Cl)Cl>[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][NH2:4].[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[NH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131732901HCID 131732901, compound

Product 1

HCID 131732900HCID 131732900, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Boc-Dap-2-AQ (11, 68.0 mg, 0.16 mmol) in CH2Cl2 (4 mL) that was stirring at 0° C. under argon was added trifluoroacetic acid (TFA, 2 mL), and stirring was continued for 2 h with warming to rt. The solvent was removed under vacuum, toluene being used to form an azeotrope with the remaining TFA. The residue, a yellow oil, was allowed to stand under diethyl ether for 1 h. Removal of the ether left a yellowish oily solid to which hexane was added and removed under vacuum until a constant weight was reached (99.4 mg; quantitative), and this material was used immediately in the next reaction.

Workup

  1. customThe solvent was removed under vacuum, toluene being

Sources & evidence

ORD record
ord-2dfbcc6455d94e5488a8de2ebefbac1b
Source dataset
uspto-grants-2015_06
Patent number
US09044518B2

Reaction notes

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